Phosphorus oxychloride → HCID 18696152, compound

HRID 1870290Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([C:21](=O)[NH2:22])[C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)=O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([C:21]#[N:22])[C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 3-(2-(N-t-butoxycarbonylamino)ethoxy)-7-carbamoyl-1,2-benzisoxazole (0.10 g) in dimethylformamide (1.0 ml) was added phosphorus oxychloride (0.06 g) with stirring at 5° C., and the mixture was then stirred at the same temperature for 15 minutes. The reaction mixture was poured into ice water (20 ml), extracted with ethyl acetate (twice each with 20 ml) and the combined extracts were dried over anhydrous magnesium sulphate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (4/1) as an eluent, to give the title compound (0.09 g, 90%) as a colorless powder.

Workup

stirringthe mixture was then stirred at the same temperature for 15 minutes
extractionextracted with ethyl acetate (twice each with 20 ml) and the combined extracts
dry with materialwere dried over anhydrous magnesium sulphate
filtrationAfter filtration
customthe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (4/1) as an eluent

Sources & evidence

ORD record: ord-c5ed596548574028b18a647a00b373d6
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06096771

Reaction notes

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